Regio- and Stereo-Selective Transformation of Glycosides to Amino-glycosides : Practical Synthesis of Amino-sugars, 4-Amino-4-deoxy-D-galactose, 4-Amino-4-deoxy-L-arabinose, 3-Amino-3-deoxy-D-allose, 3-Amino-3-deoxy-D-glucose, 3-Amino-3-deoxy-D-ribose, 3-
スポンサーリンク
概要
- 論文の詳細を見る
One of the hydroxyl groups in glycosides was regio- and stereo-selectively converted to an amino group as follows. A glycoside was regioselectively converted to an oxo-glycoside by bis-tributyltin oxide-bromine oxidation. Oximation of this and reduction of the resulting oxime in a stereoselective manner gave an amino-glycoside in a satisfactory yield.By application of this method, 4-amino-4-deoxy-D-galactose, 4-amino-4-deoxy-L-arabinose, 3-amino-3-deoxy-D-allose, 3-amino-3-deoxy-D-glucose, 3-amino-3-deoxy-D-ribose, 3-amino-3-deoxy-D-xylose, and 2-amino-2-deoxy-D-mannose were synthesized in satisfactory yields from D-xylose or D-glucose as their α- or β-methyl glycosides. The method also provided a practical synthetic route to nojirimycin (5-amino-5-deoxy-D-glucose), a glucosidase-inhibitory antibiotic, from D-glucose.
- 公益社団法人日本薬学会の論文
- 1989-10-25
著者
-
津田 喜典
金沢大学
-
津田 喜典
Faculty of Pharmaceutical Sciences, Kanazawa University
-
津田 喜典
金沢大学薬学部
-
津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
-
金光 公浩
Faculty of Pharmaceutical Sciences, Kanazawa University
-
奥野 之宏
Faculty of Pharmaceutical Sciences, Kanazawa University
-
岩城 稔
Faculty of Pharmaceutical Sciences, Kanazawa University
-
金光 公浩
Faculty Of Pharmaceutical Sciences Kanazawa University
-
奥野 之宏
Faculty Of Pharmaceutical Sciences Kanazawa University
-
岩城 稔
Faculty Of Pharmaceutical Sciences Kanazawa University
関連論文
- 糖類水酸基の一選択的修飾と変換 : スズ化合物による水酸基の選択的活性化
- Studies on Crude Drugs Effective on Visceral Larva Migrans. IV. : Isolation and Identification of Larvicidal Principles in Pepper
- Studies on Crude Drugs Effective on Visceral Larva Migrans. III. : The Bursting Activity of Tannins on Dog Roundworm Larva
- Studies on Crude Drugs Effective on Visceral Larva Migrans. II. : Larvicidal Principles in Kaempferiae Rhizoma
- Studies on Crude Drugs Effective on Visceral Larva Migrans. I. Identification of Larvicidal Principles in Betel Nuts(Pharmacognosy,Chemical)
- A Convenient Synthesis of Tertiary Amines by Alkylation of Secondary Amines with Alkyl Halides in the Presence of Potassium Hydride and Triethylamine
- Stereoselective Introduction of Oxygen Functionalities at the 11β-Position of Erythrinan Skeleton : Total Syntheses of (±)-Erythristemine and (+)-Erythrartine
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (5). Cyclization of Perhydro-2-epoxymethylene-6-oxo-6H-pyrido[2,1-i]indole-1-acetic Acid : Synthesis of 8-Oxoerythroidans
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids.(3). Synthesis of β-Erythroidine Skeleton (β-Erythroidan)
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (1). Synthesis and Isomerization of Unsaturated Bicyclic δ-Lactones
- Anthelmintic Effect of the Embelia ribes Decoction and Embelin Derivatives on Trichuris muris in Mice
- Trichuris muris : The Anthelmintic Effect of Mebendazole in Mice is Dependent upon the Pre-treatment with Steroids
- Mobility Inhibition and Nematocidal Activity of Asarone and Related Phenylpropanoids on Second-Stage Larvae of Toxocara canis
- A Tetrazorium Dye (MTT) Assay for Testing Larval Viability Using Second-Stage Larvae of Toxocara canis
- Nematocidal Activity of Turmeric : Synergistic Action of Curcuminoids
- Nematocidal Activity of Long Alkyl Chain Amides, Amines, and Their Derivatives on Dog Roundworm Larvae
- Nematocidal Principles in "Oakmoss Absolute" and Nematocidal Activity of 2,4-Dihydroxybenzoates
- Studies on Crude Drugs Effective on Visceral Larva Migrans. V. : The Larvicidal Principle in Mace (Aril of Myristica fragrans)
- Chiral Synthesis of Erythrina Alkaloids. (2). Synthesis of enantio-Type Erythrinan Alkaloids Utilizing Asymmetric Acylation and Kinetic Resolution of Diastereomers
- CHIRAL SYNTHESIS OF ENANTIO-TYPE ERYTHRINAN ALKALOIDS UTILIZING ASYMMETRIC ACYLATION AND KINETIC RESOLUTION OF DIASTEREOMERS
- 4,4-Dimethyl Effect. (7). The A-Ring Conformation of 4,4-Dimethyl-3-keto Steroids in Solution. The Circular Dichroism Spectra of Onoceranediones
- 4,4-Dimethyl Effect (2). Syntheses, ^1H- and ^C-Nuclear Magnetic Resonance Spectra, and the Conformations of 6α- and 6β-Substituted-1,1,10β-trimethyl-trans-decal-2-ones (8α- and 8β-Substituted-4,4,10β-trimethyl-trans-decal-3-ones), Models of 4,4-Dimet
- 4,4-Dimethyl Effect (2). Syntheses, ^1H- and ^C-Nuclear Magnetic Resonance Spectra, and the Conformations of 6α- and 6β-Substituted-1,1,10β-trimethyl-trans-decal-2-ones (8α- and 8β-Substituted-4,4,10β-trimethyl-trans-decal-3-ones), Models of 4,4-Dimet
- Barbaloin Stimulates Growth of Eubacterium sp. Strain BAR, a Barbaloin-Metabolizing Bacterium from Human Feces
- 4,4-Dimethyl Effect. (3). The Ring A Conformation of 4,4-Dimethyl-Δ^7-3-keto Steroids and 4,4,8-β-Trimethyl-3-keto Steroids (3-Keto-triterpenoids). The Crystal Structure of Serratenedione
- SYNTHESES OF THE β-ERYTHROIDINE SKELETON(Communications to the Editor)
- 90(P04) β-エリスロイジンの合成研究(ポスター発表の部)
- ASYMMETRIC [2+2] PHOTOCYCLOADDITION REACTION OF A CHIRAL DIOXOPYRROLINE TO 2-(TRIMETHYLSILYLOXY)BUTADIENE : CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS
- A Stable Monosubstituted Isoindole Derivative : The Crystal Structure of 1-(1,2,3-1H-Benzotriazol-1-yl)-2-(4-methylphenyl)-2H-isoindole
- REARRANGEMENT OF 2,3-DIOXO-1,4-OXAZINES TO 4,5-DIOXOOXAZOLES IN THE REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE
- Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
- Synthesis of Highly Deydrogenated Oxoerythrinan Alkaloids, Erytharbine and Crystamidine
- Dioxypyrrolines. LV. Stereochemical Pathway of [2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes
- Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions
- Dioxopyrroline. LIV. Steretchemical Pathway of[2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Acyclic Olefins
- Dioxopyrrolines. LIII.Stereochemical Pathway of [2+2] Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers
- 茯苓の研究-1-菌核の産出状況および形態
- 色彩計による生薬の品質評価-1-粉末生薬の測定条件と人参類生薬の品質評価
- Reaction of Phenylselenenyl Chloride with Δ^2-Erythrinans in Methanol : Conformational Fluctuation and Stereochemical Pathway
- Hydride Reduction of Erythrinan-7,8-diones and 7-O-Methanesulfonyl-8-oxo-erythrinans
- Synthesis and Reactions of 3,7-Cycloerythrinan : Skeletal Rearrangement of 2,7,8-Trioxoerythrinans to 4-Oxo-4H-pyrido[2,1,-a]isoquinolines
- Synthesis of Erythrina and Related Alkaloids.XXIV. Total Synthesis of Erysotrine from 1,7-Cycloerythrinan Derivatives by the Use of a New 1,2-Carbonyl Transposition Method
- Synthesis of Erythrina and Related Alkaloids. XXIII. : Intramolecular Cyclization Approach. (2). Synthesis and Reactions of 1,7-Cyclo-cis-erythrinans, Potential Intermediates to Natural Erythrina Alkaloids
- Synthesis of Erythrina and Related Alkaloids. XXII. : Intramolecular Cyclization Approach. (1) : New Synthetic Route to Erythrinan and Related Heterocycles and Synthesis of (±)-3-Demethoxy-erythratidinone
- Photo-Cycloaddition of 3-Methoxycyclohexenone and 3-Aminocyclohexenone to Ethoxyethylene : Stereochemistry of the Cycloadducts
- Studies toward Total Synthesis of Non-aromatic Erythring Alkaloids. (6). Synthesis of 8-OXO-γ-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.
- Regioselective Syntheses of Mono-O-acylglucoses
- SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD
- Regioselective Monotosylation of Non-protected and Partially Protected Glycosides by the Dibutyltin Oxide Method
- 4,4-Dimethyl Effect. (4). The Conformation of α-Onoceradienedione in the Crystalline State
- Regioselective Introduction of a Methoxy Group at the Benzylic Position of Isochromane Derivatives by Cerium(IV) Oxidation in Methanol
- SYNTHESIS OF COCCULOLIDINE SKELETON, A NON-AROMATIC NOR-ERYTHRINAN ALKALOID(Communications to the Editor)
- REGIOSELECTIVE INTRODUCTION OF p-COUMAROYL GROUP TO α-L-ARABINO-PYRANOSIDES. TOTAL SYNTHESES OF INUNDOSIDE-G AND INUNDOSIDE-D_1
- Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates
- 26 ホモエリスリナアルカロイド,(±)schelhammericine,(±)3-epischelhammericineの全合成
- TOTAL SYNTHESIS OF THE HOMOERYTHRINAN ALKALOIDS, SCHELHAMMERICINE AND 3-EPISCHELHAMMERICINE
- Conversion of Thiocarbonyl into Carbonyl Group by O-S Exchange Reaction with Dibutyltin Oxide or Bistributyltin Oxide
- Total Synthesis of Hydroxyhopanone
- Synthesis of Malabaricones, Diarylnonanoids Occurring in Myristicaceous Plants
- A NEW 1,2-CARBONYL TRANSPOSITION METHOD VIA PHENYLSELENENYLATION. HIGH YIELD TRANSFORMATION OF O-METHYLESTRONE TO O-METHYLISOESTRONE
- Infrared Spectra of Conjugated Amides : Reassignment of the C=O and C=C Absorptions
- Synthesis and Nematocidal Activity of Hydroxystilbenes
- 68 二,三の天然アシル化糖およびアシル化配糖体の合成 : 糖類に対する位置選択的アシル基の導入
- スピロ型構造を持ったアルカロイド群の全合成
- 日本薬学会奨励賞受賞森裕二氏の業績
- 白樺6大学合同セミナーなど(研究者の能力を高めるために実行している教育)
- ヒガンバナ科アルカロイドの全合成
- "薬とは何か"の化学(薬品化学で何を教えるか)
- 日本薬学会学術賞紹介-2 : 藤田栄一氏の業績
- 医薬品の開発と天然物化学(薬学領域において天然物化学研究に託される役割り)
- I-C-9 腸内細菌による和漢薬成分の代謝(第 22 報) : Eubacterium sp. BAR における Barbaloin 代謝酵素の誘導
- New Method for Isomerization of (Z)-Stilbenes into the (E)-Isomers Catalyzed by Diaryl Disulfide
- CHEMISTRY OF OXO-SUGARS (1). REARRANGEMENT OF 2-OXOGLYCOSIDES IN PYRIDINE : EVIDENCE OF INTRAMOLECULAR HYDRIDE SHIFT
- Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre
- TRIALKYLTIN RADICAL USED TO CATALYZE THE O,S-REARRANGEMENT OF CYCLIC THIONOCARBONATES. A NEW ENTRY TO THIO-SUGARS(Communication to the Editor)
- 天然由来殺寄生虫物質
- Lithium Aluminum Hydride Reduction of Glycopyranoside-Monosulfonates : Formation of Branched Furanosides
- TWO NEW GYMNEMIC ACID CONGENERS CONTAINING A HEXULOPYRANOSIDE MOIETY
- Z-E Isomerization of β-Methoxychalcones : Preferred Existence of E-Isomers in Naturally Occurring β-Methoxychalcones
- Regio- and Stereo-Selective Transformation of Glycosides to Amino-glycosides : Practical Synthesis of Amino-sugars, 4-Amino-4-deoxy-D-galactose, 4-Amino-4-deoxy-L-arabinose, 3-Amino-3-deoxy-D-allose, 3-Amino-3-deoxy-D-glucose, 3-Amino-3-deoxy-D-ribose, 3-
- Regioselective Mono-oxidation of Non-protected Carbohydrates by Brominolysis of the Tin Intermediates
- Selective Deoxygenation via Regioselective Thioacylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method(Organic,Chemical)
- Hexahydro-dibenz[d, f]azecines : Existence of Two Conformational Isomers of the 6-Oxo Derivatives in Solution
- Regioselective Monoalkylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method
- The Alkaloidal Constituents of Goda-Manel (Crinum zeylanicum L.), a Sri Lankan Folk Medicine
- A Highly Stereoselective Synthesis of rel[1R, 3R, 7R, 9S]9-Acetoxy-8,8-dimethyltricyclo[5.4.0.0^]undecan-4-one, a Versatile Intermediate to Terpenoids. Synthesis of α-Onocerin
- ^C-Nuclear Magnetic Resonance (NMR) Spectra of O-Acylglucoses. Additivity of Shift Parameters and Its Application to Structure Elucidations
- Syntheses and ^1H- and ^C-Nuclear Magnetic Resonance Spectra of All Positional Isomers of Methyl Mono-O-tetradecanoyl-a- and β-D-Glucopyranosides
- REGIOSELECTIVE MONO-OXIDATION OF NON-PROTECTED GLYCOSIDES BY THE BIS-TRIBUTYLTIN OXIDE-BROMINE METHOD
- 4,4-Dimethyl Effect. (6). The Ring A Conformation of 4,4-Dimethyl-3-keto Steroids and Triterpenoid-3-ketones : Predicted and Observed Geometries and Their Chiroptical Properties
- 4,4-Dimethyl Effect. (5). The Conformation of 8αH, 14βH-Onocerane-3,21-dione (Onoceranedione-I) in the Crystalline State
- アシル化糖の位置選択的合成とその転位 : 糖類水酸基の位置選択的修飾
- On the Possibility of Direct O-1β→ -6 Acyl Migration in 1-O-Acyl-β-D-glucose Derivatives
- General Path of O-Acyl Migration in D-Glucose Derivatives : Acyl Migration of Methyl Mono-O-myristoyl-α- and β-D-Glucopyranosides and Mono-O-myristoyl-D-glucopyranoses
- REGIOSELECTIVE OXIDATION OF A β-L-ARABINOPYRANOSIDE VIA CYCLIC TIN INTERMEDIATE. FACILE SYNTHESIS OF 4-AMINO-4-DEOXY-L-ARABINOSE, AN AMINO-SUGAR FOUND IN LIPOPOLYSACCHARIDES OF SOME SALMONELLA R MUTANT STRAINS
- Practical Syntheses of [R]- and [S]-1-Alkylamino-3-aryloxy-2-porpanols from a Single Carbohydrate Precursor
- Highly Stereoselective Grignard Reaction of an Aldopyranose : A Simple synthesis of 6-Deoxy-D-idose from D-Xylose
- 色彩計による生薬の品質評価(第2報) : 大黄の色彩と含有成分量
- ネパール産カギカズラ属植物Uncaria scandensの形態とアルカロイド成分
- 色彩計による生薬の品質評価(第1報) : 粉末生薬の測定条件と人参類生薬の品質評価